2-丁基-4-甲基-1H-苯并咪唑 | 77303-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-丁基-4-甲基-1H-苯并咪唑
• 英文名称: 2-butyl-4-methyl-benzimidazole
• 英文别名: 2-butyl-4-methyl-1H-benzimidazole；2-butyI-4-methyl-1H-benzo[d]imidazole；4-Methyl-2-butylbenzimidazole
• CAS: 77303-08-3
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: KWXMCOSRMGUVNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-丁基-4-甲基-1H-苯并咪唑 在 镍 4-二甲氨基吡啶 、 氢气 、 三甲基乙酰氯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 23.0~25.0 ℃ 、344.73 kPa 条件下， 反应 6.0h， 生成 (S) Methyl 1-[2-[[4-[(2-butyl-4-methyl-1H-benzimidazol-1-yl)methyl]phenyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Nonpeptide angiotensin II receptor antagonists. 1. Synthesis and in vitro structure-activity relationships of 4-[[[(1H-pyrrol-1-ylacetyl)amino]phenyl]methyl]imidazole derivatives as angiotensin II receptor antagonists

  摘要：

  A novel series of non-biphenylyltetrazole angiotensin II receptor antagonists which contain a 1H-pyrrol-1-ylacetyl residue in place of the benzoyl residue in EXP 6803 have been developed. The receptor binding activity of several members of this new series was in the 10(-8) M range, which was better than that of EXP 6803. Introduction of a carboxylic acid moiety at the 2-position of the pyrrole ring enhanced the in vitro binding affinity at the receptor by 10-fold. Compounds containing an acetic acid (18) or a propionic acid residue (20) at the 5-position of the imidazole were more potent than the carboxylic acid analogue (24). The binding IC50 of the most potent compound 20 was 22 nM. Compounds 18, 20, and 24 in their best fit conformations were manually overlayed on that of the template conformation of EXP 6803 and EXP 8623, respectively. The synthesis and structure-activity relationship data are described.

  DOI：

  10.1021/jm00064a007
• 作为产物：
  描述：

  原戊酸三甲酯 、 2,3-二氨基甲苯 在 氨基磺酸 作用下， 以 甲醇 为溶剂， 反应 0.9h， 以85%的产率得到2-丁基-4-甲基-1H-苯并咪唑
  参考文献：
  名称：

  高效氨基磺酸/甲醇催化体系在室温下合成苯并咪唑衍生物

  摘要：

  发现氨基磺酸/甲醇是通过 邻 苯二胺与原酸酯在室温下高收率缩合来合成苯并咪唑化合物的有效催化体系 。

  DOI：

  10.1007/s00706-006-0566-1

文献信息

• 6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: synthesis, biological activity, and structure-activity relationships
  作者：Uwe J. Ries、Gerhard Mihm、Berthold Narr、Kai M. Hasselbach、Helmut Wittneben、Michael Entzeroth、Jacobus C. A. van Meel、Wolfgang Wienen、Norbert H. Hauel

  DOI：10.1021/jm00077a007

  日期：1993.12

  reported nonpeptidic angiotensin II (AII) receptor antagonists DuP753 (1) and Exp 7711 (2), we have designed and investigated novel substituted benzimidazoles. Systemic variation of several substituents at the benzimidazole ring positions 4-7 led to the finding that substitution in position 6 with acylamino groups results in highly active AII antagonists. Compounds with 6-membered lactam or sultam substituents

  从最近报道的非肽类血管紧张素II（AII）受体拮抗剂DuP753（1）和Exp 7711（2）开始，我们设计并研究了新型取代的苯并咪唑。苯并咪唑环位置4-7上几个取代基的系统变化导致发现，位置6被酰基氨基取代会产生高活性的AII拮抗剂。在苯并咪唑的6位上具有6元内酰胺或sultam取代基的化合物在低纳摩尔范围内显示受体活性，但当口服给予大鼠时仅具有弱活性。相反，用碱性杂环类似地取代苯并咪唑部分产生有效的AII拮抗剂，其在口服后也被很好地吸收。该系列中活性最高的化合物33（BIBR 277），被选为临床发展的候选人。在分子模型研究的基础上，提出了这种新型的AII拮抗剂与AT1受体的结合模型。
• Substituted benzimidazoles as angiotensin II antagonists
  申请人：Merck & Co., Inc.

  公开号：EP0400835A1

  公开（公告）日：1990-12-05

  There are disclosed new substituted benzimidazole compounds and derivatives thereof which are useful as angiotensin II antagonists. These compounds have the general formula:

  已披露了新的替代苯并咪唑化合物及其衍生物，这些化合物可用作血管紧张素Ⅱ拮抗剂。这些化合物的一般公式为：
• Anilide derivatives with angiotensin II antagonist properties
  申请人：Warner-Lambert Company

  公开号：US05242939A1

  公开（公告）日：1993-09-07

  This invention relates to anilide derivatives of Formula I ##STR1## which antagonize the binding of angiotensin II to its receptors. The compounds are useful in the treatment of hypertension, heart failure, glaucoma, and hyperaldosteronism. Methods of making the compounds, novel intermediates useful in the preparation of the compounds, compositions containing the compounds and methods of using them are also covered.

  这项发明涉及公式I的苯酰胺衍生物，其对抗血管紧张素II与其受体的结合。这些化合物在治疗高血压、心力衰竭、青光眼和高醛固酮血症方面具有用途。制备这些化合物的方法，制备这些化合物的新型中间体，含有这些化合物的组合物以及使用它们的方法也涵盖在内。
• Water-soluble preflux, printed circuit board, and process for treating the surface of a metal in a printed circuit board
  申请人：——

  公开号：US20030141351A1

  公开（公告）日：2003-07-31

  The invention provides a water-soluble prefluxe that can solve problems with a soldering land array having a narrow spacing in that fused solder is likely to cause soldering bridges with defective soldering, a printed circuit board with its film formed thereon, and a surface treatment process for a metal in that circuit. The water-soluble preflus comprises given two different benzimidazoles compound and an iodine-based compound optionally with an amino acid, etc. The invention provides a printed circuit board with a film of that preflux formed thereon, and a surface treatment process for the metal in that circuit.

  本发明提供了一种水溶性预熔剂，它可以解决焊接地阵列间距较窄，熔化焊料容易造成焊接桥和焊接缺陷的问题，还提供了一种印刷电路板及其上形成的薄膜，以及该电路中金属的表面处理工艺。水溶性预熔剂包括给定的两种不同的苯并咪唑化合物和一种碘基化合物（可选）以及一种氨基酸等。本发明提供了一种印刷电路板，其上形成了一层该预熔剂的薄膜，以及该电路中金属的表面处理工艺。
• Sanjeeva Reddy; Nagaraj, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 7, p. 1154 - 1159
  作者：Sanjeeva Reddy、Nagaraj

  DOI：——

  日期：——